Vacation rentals in Wintergreen
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Top-rated vacation rentals in Wintergreen
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Close to hiking! | King Beds | Fireplace | Hot Tub
Welcome to Blackrock Escape! Dog friendly, 2BR/2.5BA mountain home in prime location at Wintergreen Resort. 3-min drive to the Mountain Inn. Walk to hiking trails–the Plunge Trail/Blackrock Park is only a 2-min walk. Two BRs on first floor - both with King-size Helix mattresses, smart TVs, and en suite bathrooms. Wood burning fireplace, games, puzzles, 65” smart TV in living room. Two decks w/gas grill and hot tub. Keurig K-Duo coffee maker and dishwasher in kitchen. Full-sized washer and dryer.
Endless Mountain Top Views from All The Way Up!
Our warm and inviting condo combines amazing proximity to hiking with to-die-for views of the Blue Ridge Mountains and the horizon 75 MILES distant! Our condo sits a mere 400-yd walk from the closest hiking trail and also has direct access to the ridge line walking area - perfect place for a morning stroll! This updated and modern mountain-themed space features: ✸ Newly renovated! ✸ Stocked modern kitchen! ✸ Two full bathrooms! ✸ Helix Hospitality Mattresses!! ✸ Cozy Fireplace w/ wood provided!
Hottub Ski InOut Renovated Chalet Lower Tyro Slope
Completely renovated, 3 BR/2BA chalet, located on Lower Tyro slope, just below Tequila. Rustic decor, fully stocked kitchen, high end appliances, granite counters. Open floor plan, walls of windows, mtn views. Beautiful stone fireplace, ample comfortable seating. 2 main floor Masters, each w/King bed, TV, luxurious bedding. Loft is a dedicated kids space: 2 sets of bunks, daybed w/trundle, TV & PS4. Gas grill, 6 person hot tub. Perfect ski home to host 2 Families, or a romantic couple's getaway.
Cozy Mountain Cabin
Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Spacious sleeping loft. Perfect romantic escape, friends getaway, or personal retreat. Workout area/sitting room. Fresh eggs (in season), wine, tea, coffee. 1G Internet, SMART TV. A/C. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from App. Trail, Wintergreen Resort, breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, & antique shopping.
NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10
We had to create a new listing for this property. Previous listing had 70+ reviews with a 4.8 Star rating. Same great host and same great house, just a new listing. Screenshots of old listing in additional photos. Stay at this luxurious 4-bedroom, 3-full bath vacation rental home for 10 in Wintergreen, within minutes of top-notch golf courses, skiing / snow boarding at the Mountain Inn, and dozens of hiking trails . In addition to the unbeatable location, the property offers a private hot tub!
Luxury Condo in the Sky! Finest in Wintergreen!
Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just a stone’s throw from nature’s bounty. Our condo offers the perfect blend of relaxation and access to recreation. Hit the ski slopes, take a hike, or explore the bountiful brew and wine scene and then come enjoy the view. The horizon is 75 miles distant from our balcony on a clear day! We love hosting families with kids or couples coming to enjoy all that Wintergreen offers!
Blue Ridge Bliss - For family & friends to enjoy!
Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.
Cliffs Edge -A Contemporary Mountain Home
An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.
1 bedroom condo, close to hikes & breweries & pool
Cozy 1BR Wintergreen condo 🌳 🌄 Close to scenic hikes, local breweries and wineries. The resort village, and mountain-top market, just minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax after a day outdoors and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and or cool off in the heated community pool.
BlueRidge Getaway- Dog Friendly
Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!
The Sanctuary
Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!
Panoramic Sunsets Mountain Views Pool $99 Midweek
SUMMER SPECIAL! Stay 2 nights and get your 3rd night for just $99 when you check in Sunday–Wednesday (select stays, next 60 days). Escape the summer heat and enjoy cooler mountain temperatures, central A/C, a heated outdoor pool, breathtaking sunset views, and two king suites with private en-suite bathrooms. Summer dates are filling fast—book now and experience one of Wintergreen's most sought-after mountain-view condos.
Popular amenities for Wintergreen vacation rentals
Other great vacation rentals in Wintergreen
Mountain View | Hot tub | Sleeps 14
Best Blue Ridge Views at Sunrise over Wintergreen
Blue Ridge Cottage - 3 Miles to Wintergreen
Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat
Cabin · Hot Tub + Sauna · Arcade · Game Porch
Wintergreen Mountain Views - Diamond in the Slopes
Natural Living in a Bell Tent
Saltbox at Wintergreen, a Modern Mountain Escape
Frequently Asked Questions
What are the best places to stay in Wintergreen?
Stay in mountain-view vacation homes, condos, or cottages near recreational areas. Properties around Wintergreen’s main resort area often feature amenities like pools, access to trails, and terraces.
What are the best things to do in Wintergreen with kids?
Kids can enjoy outdoor adventure programs, guided nature walks, and swimming in resort pools. In winter, snow tubing and beginner ski lessons are often recommended activities for families.
What are some of the best things to do in Wintergreen?
Explore hiking trails, enjoy skiing or snowboarding in cooler months, and play golf in warmer seasons. Visiting local breweries, shops, and participating in mountain festivals is frequently suggested.
How is the weather in Wintergreen?
Wintergreen has cool winters around 28–44°F (-2–6°C), and warm, humid summers reaching 68–84°F (20–29°C). Rainfall is spread throughout the year, so a waterproof layer is often useful for outdoor plans.
When is the best time to visit Wintergreen?
Mid spring through early fall is often recommended for mild temperatures and vibrant mountain scenery. If you enjoy winter sports, colder months bring snowfall and opportunities for skiing or snowboarding.
What are the best places to visit in Wintergreen?
Wintergreen has scenic overlooks, mountain hiking trails, and golf courses that attract visitors. Local breweries and shops add to the experience, especially around the main resort area.
What are some hiking trails in Wintergreen?
Explore forested trails with mountain views; paths around the main resort area frequently offer scenic overlooks and waterfalls. Trail networks cater to a range of abilities, from gentle walks to steeper climbs.
What are some family activities we can do in Wintergreen?
Families can explore nature trails, play mini golf, or participate in outdoor adventure programs. Seasonal activities include snow tubing in winter, swimming in warmer months, and craft workshops around local festivals.
What are some of the best day trip ideas from Wintergreen?
Popular day trips include exploring nearby vineyards, visiting small mountain towns with craft galleries, or hiking in regional parks. Local farm tours and river kayaking are frequently suggested for adventure seekers.
Are there any pet friendly accommodations available in Wintergreen?
Several accommodations in Wintergreen welcome pets, often around the main resort and near hiking areas. Outdoor amenities and easy access to trails make it convenient to travel with your dog.
What are some local tips for visiting Wintergreen?
Bring layers for changing weather and plan ahead for outdoor activities, especially in peak seasons. Locals suggest visiting mountain overlooks early in the morning for quiet scenery, and sampling craft food at neighborhood markets.
What is Wintergreen known for?
Wintergreen is known for scenic mountain landscapes, outdoor recreation like hiking and skiing, and golf courses. Locally rooted food and craft beverages are frequently suggested throughout the area.
What are the best hidden gems to explore in Wintergreen?
Discover tucked-away hiking paths, local artisan shops, and quiet picnic spots around the mountain. Insider tips often highlight farm-to-table dining and scenic overlooks that are less traveled.
What are the best foods to try in Wintergreen?
Wintergreen’s dining features locally sourced mountain cuisine, including roasted meats, farm-fresh vegetables, and craft beverages. Seasonal menus often highlight apple desserts, regional cheeses, and handmade breads.
What should I bring for a trip to Wintergreen?
Pack layers for changing mountain conditions, comfortable hiking shoes, and a waterproof jacket. If visiting during cooler months, bring warmer clothing; in summer, sunscreen and a hat help for outdoor activities.
What is the nightlife in Wintergreen like?
Wintergreen’s nightlife centers on casual venues with music, craft beverages, and locally rooted dining. Social gatherings often feature scenic mountain views and relaxed atmospheres.
What are the most popular events or festivals in Wintergreen?
Wintergreen has seasonal festivals, including events for music, arts, and food. Outdoor celebrations around Labor Day weekend and winter gatherings with snow sports are frequently suggested.
Are there family friendly vacation rentals in Wintergreen?
Many vacation rentals in Wintergreen are equipped for families, often featuring spacious layouts, kitchen access, and outdoor amenities. Look for options near recreational areas and trails for easy access to activities.
All about Wintergreen
Sitting on the eastern slopes of the Blue Ridge Mountains — which are part of the Appalachian Mountains — is the Virginia destination of Wintergreen. Located about 40 minutes southeast of Charlottesville, the area is known for its wide-ranging elevations, from the deep valley floors to the majestic mountaintops. The community was built as a golf destination in the spring and summer and as a winter sports hub in the snowy months, making it the perfect mountain escape any time of year.
What are the top things to do in Wintergreen?
Outdoor Sports
From the beginning, Wintergreen was conceived as a year-round destination, with its golf resort opening in 1988 and its ski facilities opening a year later. Nowadays, those teeing off have a choice of two courses at Devils Knob and Stoney Creek, while skiers and snowboarders can choose from 24 trails, including 14 that are lit for night skiing. There’s also a 900-foot snow tubing hill and an ice skating rink that can hold 60 skaters. Other activities include tennis, boating, biking, hiking, ziplining, and flying high on the floating trampoline.
Rockfish Valley Trails
Five trails run through the south fork of Rockfish River and Reid’s Creek with six miles of pathways that are popular with hikers and birdwatchers. There are parking lots at the Rockfish River trailhead, as well as the 35-acre Spruce Creek Park, the only public park in Nelson County.
Skyline Drive at Shenandoah National Park
From Wintergreen, it’s about a 20-minute drive to the northern entrance of the Blue Ridge Parkway, Rockfish Gap Entrance Station. This is also the southernmost entrance point to the national park’s historic Skyline Drive, where the 105-mile stretch has its final mile marker near Waynesboro. From there, the scenic road stretches north along the crest of the Blue Ridge Mountains up to the mile marker 0 in Front Royal.
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- Shenandoah National Park
- University of Virginia
- Early Mountain Winery
- Wintergreen Resort
- James Madison University
- Monticello
- Devils Backbone Brewing Co Basecamp
- Glass House Winery
- Natural Bridge State Park
- Blenheim Vineyards
- Virginia Horse Center
- Cardinal Point Winery
- The Rotunda
- Liberty Mountain Snowflex Centre
- John Paul Jones Arena
- Frontier Culture Museum
- James Monroe's Highland
- Downtown Mall
- Amazement Square
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- White Oak Lavender Farm & The Purple WOLF Vineyard
- IX Art Park
- White Lotus Eco Spa Retreat
- James River State Park